New England Travel Guide

Let me just start by saying that this trip was the trip of a lifetime – it was one for the books, in more ways than one! I have always wanted to visit New England, but especially New England in the Fall! And, we did New England the right way – we visited Vermont, New Hampshire, Maine, and Massachusetts (Salem and Boston). We did, saw, and ate everything we wanted and we didn’t hold back and feel that we got a great taste of New England, even if the trip was only 5 days!

One downfall, and something I don’t recommend doing, is driving through the night (which we did)— we left VA Beach around 2-3 AM on Sunday/Monday and arrived in Waitsfield around 8 PM that Monday night. It was unbelievably tiring and we had to stop for a 2-hour nap on the way. BUT, it was totally worth it!!! We preferred to drive rather than fly because I had A LOT of luggage and we were traveling all over, so we felt it would be easier. Also, we got to drive through upstate New York and it was beautiful. We also got to stop by the cutest drive-thru coffee shop (@lumbarjackscoffee) on the NY/VT border—their cider donuts and maple lattes were ones for the BOOKS.

Get the Look

Get the Look

In Vermont, we stayed at the historic Inn at The Inn at Round Barn Farm in Waitsfield—it’s the cutest little town and so close to Warren Falls, and only a short drive to Stowe. That evening, when we arrived, we explored our little inn and then called some local places to see what was still open for us to grab a bite—we went to a little sports bar in town and it was surprisingly delicious! I don’t even remember what it was called...we were so tired and it was the only place with the kitchen still open! After a late dinner, we went straight to bed since...exhausted does not even cover it! The following morning, we woke up so refreshed and had the BEST breakfast at the inn (peep the deliciousness in the video)—the eggs were made to order and SOOOO yummy! After breakfast, we walked and explored around the inn and drove up the road to admire the view. We, then, ventured to Warren Falls—we were one of the only ones there and it was magical! It gave me all the Iceland flashbacks! For lunch, we had hot apple cider and apple cider donuts from Cold Hollow Cider Mill, a charming little spot that also has a market for maple syrups and other Vermont goodies. From there, we drove up to Stowe and explored the little town. We walked the nature trail behind the white steeple church and it was absolute perfection...the views, the temps, just everything.

Get the Look

From there, we had about a 2.5+ hours drive to Bedford Village Inn in New Hampshire. You guys, this place is seriously STUNNING! Our suite at The Grand had a fireplace and a HUUUGE, majestic soak tub (which I took full advantage of)! You can check out my IG highlights for BTS of our stay. The lobby and bar at The Grand are SOOO COZY—it’s got a massive stone fireplace and the vibes are like that of a high-end cabin in the mountains. Their breakfast is also SOOOO delicious—they have a full breakfast bar and it is so fun to bring your work downstairs and eat/work by the fireplace, which is exactly what we did. We stayed here for two days and loved every second!

While in New Hampshire, we went up to southern Maine since it was so close (that’s the great part about New England...everything is relatively close)! We knew we would regret not seeing at least one lighthouse while in New England, so we drove to Nubble Lighthouse and it was absolute perfection—so picture-perfect, I felt like I was in a painting or a movie scene...just WOW! This was probably one of our favorite places! Everything about it was so idyllic and what you think of when you think of the New England coast! After climbing the rocks and exploring Nubble, we got pretty hungry, so we scoped out the best lobster and clam chowder and we traveled a little more north to Ogunquit, where we grabbed some yummy lobster rolls and clam chowder from the cutest lobster shack in Perkins Cove called The Lobster Shack (family-owned for generations, low ceilings, tiny windows, and the sweetest people with the best food...just the best)! The location is great because there are so many quaint, little shops around too!

Get the Look


From New Hampshire and Maine, we made our way south to Massachusetts. First stop was Salem because I wanted to see the Hocus Pocus/Witch house and just explore the historic town. Honestly, other than the organic juice place (Life Alive) we stopped at and the Hocus Pocus house, Salem was a strange town—lots of freaky people, especially because we were there so close to Halloween. Overall, it felt like a very dark place and it was WAY. TOO. CROWDED. I am convinced crowds and lines are from the devil, so even just those things make me question a place...LOL

ANYWAY. From there, we made our way to our hotel in Boston. We stayed at Yotel in Seaport (seriously, the BEST location ever) and the hotel is like an airplane! The rooms are called cabins and they’re designed to be efficient and really bring back the space/flight vibes from back in the 60s (they really liked the futuristic stuff back then [think Jetsons]). Yotel is centrally located and so close to awesome restaurants and shopping (we had Lululemon and Sephora across the street [did you know there is no sales tax in Boston?! Mama was happy, let me tell ya!]). We parked our car with the valet and walked and Ubered everywhere in Boston. We loved Boston so much that we are seriously considering moving there after we’re done with law school. For real, for real.

WHILE in Boston, we had our coffee and ate breakfast every morning at Tatté (cutest little bakery and healthy, tasty meals). This place is legit IG worthy and it’s yummy too, DOUBLE WIN! Other yummy places we enjoyed are Legal Seafood (for the yummiest, freshest seafood around), Mike’s Pastry (for the BESSSSSSSSSST cannolis on the planet [not one ounce of exaggeration there]). Bring cash; they don’t accept cards. Because we forgot cash, I went across the street to take out cash and forgot my debit card in the ATM. Thankfully, after a handful of seconds, the machine sucks the card back in. So, when I called the bank the following morning, they had my card! Woohoo! Don’t be me—come prepared with cash. The line is worth the wait, I promise; it’s honestly the only line I’m willing to wait in. LOL! I had the Nutella cannoli and Parker had the amaretto—we were extremely satisfied with our choices...DELICIOUS. We visited Acorn Street (most photographed street in the US) Harvard, Boston Common, and shopped at Copley Square (that’s where I picked up my beautiful Louis ONTHEGO, which I am STILL obsessed with)! Our favorite part was how walkable the city is and just the overall’s a cleaner, smaller, (dare I say better???) NYC and I was all about it!

Get the Look

Get the Look

Get the Look

We had the best time on the trip, and it checked off a bucket list item (Fall in New England). It was everything and more than we could’ve wanted. It was sufficiently planned that we were not disorganized, but not so planned that we couldn’t deviate and explore where/when we wanted.

Love y’all and I hope this itinerary is helpful in planning your New England trip! Email me if you have any specific questions!

Catch ya next time! Kisses, Besos, Pupici!

You may also like

Leave a Reply

Your email address will not be published. Required fields are marked *